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Social media's favorite menswear guy on the dos and don'ts of the pocket square


I am a man who likes a pocket square, that small flourish of fabric that goes in the pocket of a suit jacket or a blazer. In fact, I feel nearly naked without a pocket square - well, not with pajamas. So it didn't escape notice at WEEKEND EDITION that menswear writer Derek Guy has been imparting wisdom about the do's and the don'ts of pocket square fashion. Derek Guy of the blog "Put This On" joins us from San Francisco. Thanks so much for being with us.

DEREK GUY: Thank you so much for having me.

SIMON: Silk, cotton or linen?

GUY: Most of my pocket squares are a wool-silk mix, but I think wool, silk, cotton or linen - all of them work, depending on the outfit and what you want.

SIMON: Patterns, prints or stripes?

GUY: The pocket square should be patterned, but should be a distinct design that's not used for shirts, jackets, and neckties. There are many companies that make unique prints for pocket squares. And even if no one sees the pattern, I think having a distinctive pattern kind of makes it look like you didn't just cut up a piece of fabric and stuff it into your pocket.

SIMON: You wrote on X, or Twitter, a pocket square should never match the tie too closely. Well, why not?

GUY: Well, you know, it kind of goes back to a very basic idea in men's dress and, as overused as the word may be, this idea of sprezzatura, of effortlessness. And if your tie and pocket square match too closely, like, if they're made from the same fabric - let's say if you are wearing a blue, pin-dot tie, I don't think you should wear a blue, pin-dot pocket square. Both because it looks like you bought them in a kind of like box set from Amazon or one of those stores that supply high school students with prom clothes.

It also looks a little bit too contrived. It looks like you, like, really thought about this and put this outfit together. When a pocket square doesn't exactly match the tie, but rather complements the tie, it creates a pleasing visual effect. But it also looks like you just threw this random accessory into your pocket and it happened to look good.

SIMON: That was what I was always told when I worked the holiday season in the menswear department of Marshall Field's.

GUY: (Laughter).

SIMON: The idea of a pocket square was to look effortless, like the last thing you do before you go out the door.

GUY: Right. It's also one of the reasons why I don't think you should fold it into these kind of like origami shapes. It should just be something you stuff into your pocket.

SIMON: Any practical purpose to a pocket square?

GUY: No. It's just decorative. Men especially try to find reasons for something. So sometimes a hat will feel less contrived if you have a reason to wear a hat, for example, like the weather. But you know a lot of things in men's clothing is just decorative. A silk necktie - which is quickly disappearing - is purely a decorative thing. And a pocket square is just purely decorative.

SIMON: Is there a resurgence of pocket squares?

GUY: I hate to say it, but I don't think there is. There was for a brief moment, about 10 or 15 years ago, when tailoring was kind of coming back. It is notable that President Biden is - wears a pocket square most of the time, and I suspect will be the last U.S. president to wear a pocket square with any regularity.

But they are, for the most part, disappearing - one, because tailored jackets are mostly disappearing. And then of the people that wear tailored jackets, only a small subset will wear a pocket square. But I am with you in that I think a tailored jacket looks better with one. The area on your chest looks a little bit blank, especially if you're not wearing a tie. If you're not going to wear a tie, then I definitely think you should wear pocket square just to have a little bit of flourish.

SIMON: Derek Guy of the fashion blog "Put This On." Thank you so much for being with us. And may all your pocket squares square up.

GUY: Thank you again for having me.


THE KINKS: (Singing) Dandy, dandy, dandy. Dandy, you know you're moving much too fast... Transcript provided by NPR, Copyright NPR.

NPR transcripts are created on a rush deadline by an NPR contractor. This text may not be in its final form and may be updated or revised in the future. Accuracy and availability may vary. The authoritative record of NPR’s programming is the audio record.

Scott Simon is one of America's most admired writers and broadcasters. He is the host of Weekend Edition Saturday and is one of the hosts of NPR's morning news podcast Up First. He has reported from all fifty states, five continents, and ten wars, from El Salvador to Sarajevo to Afghanistan and Iraq. His books have chronicled character and characters, in war and peace, sports and art, tragedy and comedy.